• There were so many Arrow man advertisements that the fictional model received fan mail.  See more examples at Fine and Dandy Shop.

$54, available in November at Urban Outfitters

Arrow Shirts

Established back in 1851, the Arrow menswear brand is one of the oldest in the country. It was also one of the most successful. Created by Cluett Peabody & Co. on the banks of New York's Hudson River, the label really took off in the early 1900s when the "Arrow Collar Man" was drawn by illustrator J.C. Leyendecker for a series of advertisements that would continue boosting sales well into the 1930s and raise the character to icon status. And while the Arrow label may've slipped into relative obscurity, Urban Outfitters is reviving it with a six-piece capsule collection. The line is comprised of vintage styles culled from the Arrow company's archive with the authentic fabrics, cut and collars of the originals.